3-Chloro-6-(pyridin-2-yl)pyridazine → 3-(6-Methylpyridin-2-yl)-6-(pyridin-2-yl)pyridazine

HRID 574189Notes

Reaction equation

HRID 574189 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([Sn](CCCC)(CCCC)CCCC)[CH:5]=[CH:4][CH:3]=1.Cl[C:22]1[N:23]=[N:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[CH:26][CH:27]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([C:22]2[N:23]=[N:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:26][CH:27]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 64179603-Chloro-6-(pyridin-2-yl)pyridazineHCID 114631832-Methyl-6-(tributylstannyl)pyridine

Product 1

HCID 64179693-(6-Methylpyridin-2-yl)-6-(pyridin-2-yl)pyridazine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The 3-(6-methylpyridin-2-yl)-6-(pyridin-2-yl)pyridazine 44 was prepared according to the general Stille coupling method, starting from a mixture of 2 g (5.23 mmol) of 6-methyl-2-tributylstannylpyridine 22, 666 mg (3.49 mmol) of 3-chloro-6-(pyridin-2-yl)pyridazine 8a, 208 mg (0.18 mmol) of tetrakis(triphenylphosphine)palladium(0) and 50 ml of freshly distilled toluene. The reaction medium is stirred at reflux for 18 h. The residue obtained is chromatographed on silica gel (eluent: ethyl acetate/petroleum ether=2/8). The coupling product 44 is isolated with a yield of 90%.

Workup

  1. customThe 3-(6-methylpyridin-2-yl)-6-(pyridin-2-yl)pyridazine 44 was prepared
  2. temperatureat reflux for 18 h
  3. customThe residue obtained
  4. customis chromatographed on silica gel (eluent: ethyl acetate/petroleum ether=2/8)

Sources & evidence

ORD record
ord-ab76b00be2fb410f8a234b5951c772bc
Source dataset
uspto-grants-2015_05
Patent number
US09034873B2

Reaction notes

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